Rachel Bilson and Hayden Christensen
![Rachel Bilson Hayden Christensen, Smile, Coat, Tie, Gesture]()
Though in this case, both teen drama actors managed to find love. Not long after her time in The O.C., Bilson met Christensen on the action movie set Jumper and they continued dating off and on for several years from that point.
Brad Pitt and Gwyneth Paltrow
![Brad Pitt Gwyneth Paltrow, Vision care, Sunglasses, Goggles, Fashion, Eyewear, Motor vehicle, Automotive design]()
Before meeting the love of his life, Pitt was dating Paltrow for a few years before the couple got engaged. The two broke up in 1997.
Angelina Jolie and Billy Bob Thornton
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The two met up in 1999’s Pushing Tin but didn’t start dating until 2000. They married after a few months, but divorced in 2003.
Brad Pitt and Angelina Jolie
![Angelina Jolie Brad Pitt, Smile, Hairstyle, Facial expression, Human, Gesture]()
Of course with an extensive list as this, it makes sense to put this couple here. Though at the time of them getting married, both of them were still married. Pitt was married to Jennifer Aniston at the time and finalized the divorce in 2005. Jolie filed for divorce much later in 2016 with her partner, two years after the two officially married in 2014.
Jennifer Aniston and Vince Vaughn
![Did Jennifer Aniston And Vince Vaughn Date, Glasses, Hairstyle, Goggles, Facial expression, Sunglasses, Vision care, Human, Hat, Fashion, Eyewear]()
Shortly after the divorce with Pitt, Jennifer started to date Vince Vaughn in 2005 after meeting on the set of The Break-Up.
